Regan managed to stall one of his evictions for eight months by appealing to the Superior Court of Ontario. (Photo: REUTERS/Shannon Stapleton)

Stories about professional tenants, sometimes referred to as “tenants from hell,” are unfortunately plentiful.

Such is the case with James Regan, a Toronto, Ont. man described as a “well-coiffed, professional tenant” who hasn’t paid rent for three luxury apartments he occupied throughout the city since 2014.

He has now been issued an eviction notice, his third in two years, for an expensive apartment he has occupied in the Yorkville area since July. The Ontario Landlord and Tenant Board ruled on October 13 that if he doesn’t pay his landlord $10,000 in rent he owes by October 24, he has to leave the premises.

How did he get away with not paying rent for so long?

Regan managed to stall one of his evictions for eight months by appealing his eviction order to the Superior Court of Ontario. This allowed him to live rent-free because the Ontario Residential Tenancies Act allows tenants to go to court to appeal an eviction order issued by the board. While the appeal is ongoing, the tenant cannot be evicted from the premises.

Regan’s current landlord could have likely avoided the problems with his problem tenant had he done a background check on him, which would have revealed his credit issues.